If an in-house lawyer needs to escalate a legal issue to the executive team, it can help to get a senior person on the business side to champion the matter, says David Sclar, interim vice president of operations and compliance at healthcare payments company Truemed. 

“When I have a hot legal issue, I don’t want to step on toes so I look for where the business is going to be affected and I get someone from the business with some seniority hopping mad about it and let them escalate it,” Sclar said in a webcast hosted by LinkSquares Chief Legal Officer Tim Parilla. “Make the legal issue part of the conversation but not the only reason we’re meeting with leadership.”

It’s rare that an issue should be escalated to leadership purely as a legal matter, said Sclar, who started as a specialist in healthcare regulatory compliance at Ropes & Gray and then Cooley before moving in-house and broadening his focus to privacy and other areas of importance to technology companies in the healthcare space. 

In-house lawyers are service providers, so they’re most effective keeping legal issues tamped down so the business can move forward with its goals, he said. When an issue arises that needs executive attention, it’s essential for counsel to offer solutions and package the choices so executives can choose the proper path. 

“Bringing solutions and not just spotting issues isn’t complicated as a concept, but as a reality, it’s a really hard soft skill,” said Sclar. In 2021, he compiled best practices for in-house counsel into a handbook, Workplace Strategies for Technology Lawyers. 

“People want useful, practical tips to do their job well, but there aren’t a lot of those for in-house lawyers,” he said.  

Junior lawyers at law firms are conditioned to spot legal issues and raise them with partners, but the dynamic is different in-house, he said.

An in-house lawyer raising a legal issue that can be handled without involving the executive team doesn’t go over well with leadership, and it’s especially bad form for a lawyer to go above someone’s head to alert a higher-up about an issue. 

“Junior lawyers coming in-house might do that reflexively because they want to solve the problem quickly,” he said. “It’s coming from a good place, but it can burn a bridge.”

Nor should in-house counsel necessarily prioritize being right over being effective, he said. 

As much as you might want to let everyone know you saw a problem coming and tried to alert people to it, if you do that without regard to how you make others look, you can alienate yourself from the team and lose their trust, he said. 

In one situation he was involved in, Sclar raised an issue with the executive team in an email chain only to have the CEO, later in the same email chain, ask him why they weren’t alerted to the problem.  

“I wanted to shout from the rooftop, ‘Hey, I didn’t mess up,’ but you can’t do that,” he said. “You’re a service provider and you’re in the business of making other people look good. You can’t have an ego. It doesn’t matter if you worked at a big fancy law firm before. Nobody cares.”

A good way to approach a potential legal issue is by guiding business leaders with questions about what they’re trying to accomplish and let them discover the risks they face so they can see the need to adjust without counsel having to tell them. 

“You have to go fishing but do it in a way that’s deferential and respectful rather than as a deposition,” he said. 

Counsel might even end up changing their mind about what to recommend from a legal standpoint, based on learning new information about what the business is trying to do.    

“When I’m raising a hard issue to business colleagues, it’s an accordion type of situation where, although I have a perspective on it, I’m prepared to go wide,” he said. “I want an open discussion. I’m not taking issues off the table. But then my job is to bring it home and distill what everybody came up with into two or three paths — A, B and C, with trade-offs – and offer the business a clear decision that they can sink their teeth into.”

Taking the opposite approach and raising a legal risk without understanding the business goal or not offering possible solutions is to create the very thing in-house counsel are expected to protect the business against: chaos. 

“So much of our job is to keep those chaotic situations from happening,” he said. 

“Getting angry and petty and going in all directions [when you have 20 people on a hair-on-fire] email chain is a dangerous situation,” he said. “Legal should never be the source of the escalation. Don’t start the fire yourself. Fires are hard enough to put out.”